Betting on a Player
by LittleMusicLover
Summary: Bets between friends are a common part of highschool. Egged on by Misty, new girl Leaf makes a bet she can go on more dates than Gary, in an attempt to lower his ego to a bearable level. The results, no one could predict. LeafGreenShipping with a little Pokeshipping thrown in.


_**Betting on a Player**_

"Gary, you are such a player, did you know that?"

"Dearest Misty, it's not my fault I was created with a manly figure and luscious locks, not to mention the irresistible eyes that no girl can ignore."

"I managed to do it."

"Misty, you are not a normal girl. You're going out with Ash."

They continued to bicker, before Ash finally managed to cut in, "Misty, do you really need to inflate his ego even more? Gary, quit it before she hits you."

"You're no fun, Ash."

Nevertheless, Gary stopped his debate with Misty, seeing her get an evil glint in her eyes. He subconsciously rubbed his arm; it had been the victim of one of Misty's punches earlier in the day. The girl was strong, there was no doubting that.

He continued to eat his lunch in silence, as Misty and Ash quietly conversed, heads close together, occasionally laughing softly.

"Get a room."

Misty looked up and arched an eyebrow at Gary. "Don't you have a girl to go hit on?"

"Hey, isn't that the new girl?" That was Ash.

A girl with brunette hair had just walked into the cafeteria. She frowned slightly, trying to find a spare seat on which to sit.

"Yes, Misty, that lovely brunette who just walked in."

He got up to go and left to meet her.

"No, Gary! Don't hurt her. She doesn't know about you yet!" Misty called, desperately.

Gary turned around and backpedalled a few steps. "You told me to."

"You kind of did, Mist."

He shut his mouth when Misty sent a glare in his direction.

"Sorry."

_**Pokémon**_

"Hey there. The name's Gary. Gary Oak."

Leaf looked towards the voice, just in time to see a hair flick followed by a flash of teeth.

"Is that supposed to impress me?"

He shrugged. "If you want it to. I can do better though."

"Really? How so?"

"Come have lunch with me?" Gary asked, nodding to a table. There were two people at it – Leaf assumed these were his friends.

She replied with a shrug of her own, and a cute, little smile. She noticed that the corners of Gary's mouth twitched at this.

He took her arm, to which she rolled her eyes, and led her to the table.

"Misty, Ash this is…" Gary trailed off, his mouth still open as he looked at Leaf, asking a silent question.

"Leaf Green," she said.

"Gary!" Misty cried. "You didn't even get her name."

"Alright, alright. I forgot. Happy?" He asked.

Leaf giggled, catching Misty's attention. "Do not giggle at that, Leaf. Gary is a player."

"Really?" Leaf narrowed her eyes at Gary. She had assumed something along those lines, but now it was confirmed.

"I am not."

"Fine, but he's gone on dates with more girls in our grade than appropriate. You're new, so I'll forgive you for laughing at him. But do not fall for his charm."

"Ha!" Gary cried. "So you do admit I have charm."

Misty ignored him. "And he dumps the girls in an inappropriate manner. It's a wonder he has any friends at all."

"You're friends with him?" Leaf asked.

"I'm dating Ash. Gary was friends with him first. We have a love-hate relationship."

Leaf nodded her understanding.

"What he needs," Misty continued, "is for his ego to be taken down a peg or two. All the girls just go on dates with him because they think he's hot. The guys can't really stand him."

"So, if I were to ignore him, his ego would be taken down a peg or two, then?" Leaf asked curiously, a mischievous look on her face.

"No, Misty, stop. What if I do really like Leaf? You're going to turn her off me before she even knows me." Gary cut in.

"You met me two seconds ago," Leaf retorted, "I don't think you can say you really like me yet."

"And Gary, I don't think you're the only one that has their eye on Leaf," Ash commented.

"What?" Gary and Leaf both blurted. They looked around the cafeteria, both seeing the looks that some of the guys were giving Leaf. She responded with a flirtatious smile and wink, Gary with a cold glare.

"What if," Leaf began, "we have a little bet?"

Leaf could see she had piqued the attention of all three of her new potential friends. This was the reaction she had been hoping for.

"I bet I can be a slut like you," she said, eyeing Gary. "If I lose, I'll go on a date with you. If I win, you have to give up dating for, let's say, a month."

Misty had a wide grin on her face. Ash was slowly shaking his head.

"Bring it on," Gary replied.

_**Pokémon**_

"This is really hard for me to do."

"You don't want to go on another date with me. I get it."

"No! It's not that. Well, it is but…"

"It's okay, Leaf," said Vince. "We're in highschool, things don't have to work out."

Leaf whispered, "I'm really sorry."

Leaf watched as Vince walked off to his home. It had been really nice of him, to walk her home. She smiled sadly. This was only the first of many people she would have to say no to.

"It doesn't get easier," came a voice.

"Are you a stalker or something?" Leaf asked, seeing Gary appear. "And besides, what would you know? You are constantly going between girls."

"That doesn't mean I like the breaking up part," he shot back.

"Then why do it?" she asked, turning and entering her house, shutting the door in his face.

"Just go on a date with me and it'll all be over!" he called through the door.

Leaf ignored him and continued up to her room. "Why do you do it, Leaf?" she asked herself.

_**Pokémon **_

"Tyler said to thank you for the movies."

It was in the middle of a school day. Leaf was collecting her books from her locker. "Did he?" she queried, nonchalantly. "That was nice of him."

"You can stop any time you want," Gary said.

"But then I would have to go on a date with you," Leaf replied.

"Would that really be so bad?"

Leaf shut her locker door, and leaned on it, facing Gary. "It really would. I'm not going to let you shoot me down like the rest of the girls you do it to."

"Like you're doing to all those guys you're dating?"

Leaf sighed. "I don't shoot them down. Besides, I think the whole school knows about our bet now since I told Liam why I couldn't go on another date with him. They go out with me knowing what they're getting into."

"I'm pretty sure that's against the rules of the bet."

"There was no fine print," Leaf replied, walking to her next class.

_**Pokémon**_

Leaf was lying on her bed, mentally counting the amount of dates she had had in the past four months.

"How much longer am I going to have to keep doing this?"

"Honey, you're nowhere near the rate Gary has with his dates."

Misty was sitting at Leaf's desk, doing some English homework. She swiveled around to face Leaf.

"Why do you say you would do this? You clearly aren't cut out to be a slut."

"Did you ever think I was? I just really wanted to make friends with you guys. I didn't actually consider what I was saying. I have a habit of doing that." She shrugged apologetically at Misty.

"At least none of the guys at school hate you," Misty sighed. "Although I still don't get why you sent Tom that signed football. You're not supposed to make them remember you with something."

"I had to!" Leaf protested. "He seemed so sad when I said I couldn't go on any more dates with him. And I know he loves football. It seemed appropriate. It distracted him."

"You really have no idea, Leaf." Misty rolled her eyes.

"So, how much longer am I going to have to keep doing this?"

Misty frowned. "I don't know. You never put a date in the bet."

They both sat in silence for a few moments before Misty started talking again. She spoke slowly, as her thoughts collected themselves. "What you need, is a really, really good date and let down. Something that Gary can't compete with."

"Like what, Misty?"

_**Pokémon**_

"Wow."

Leaf jumped. She turned to the voice, and saw Gary. She felt a slight blush come to her face, and she looked down at the floor.

Her dress was skintight, which was probably what Gary had first noticed. He could be such a pervert sometimes.

"Who are you dressing up so pretty for?"

She looked back at Gary and flashed her best smile. It turned out more of a grimace though. "James. He's in my Biology class."

"Wow," Gary repeated. "You should dress like that for our date."

"Who said we're having a date?"

"Leaf, don't try to bluff this out. You're not a slut. You'll be having a date with me soon enough. That, or you just won't be able to resist my charm any longer. Really, it's a win win."

"It's really not," Leaf replied.

"So you like dating random guys?" he asked.

"They know what they're getting into," she mumbled. As much as she tried to convince herself of this, even Leaf did not think that what she was doing was fair.

"You could get out of it."

"I'm well aware of that, Gary." Leaf said, annoyed.

She stalked off down the road. It really did amaze her how Gary seemed to turn up whenever she was leaving for, or arriving back from, a date. He was really persistent. Leaf liked that.

But no, she was doing this for a better cause. It was true, the dates had been bringing her down. She hated going out with someone just to break up with them soon after. But this was the only way she could prove the point to Gary.

She needed to be her perkier self again. Leaf plastered a smile on her face. There, that was better. Already, she felt happier. It would not be long now. Then this would all be behind her.

_**Pokémon**_

"Misty, I cannot take this any longer!" Leaf cried, sobbing.

She was sitting on Misty's bed, in Misty's house.

"I know, honey, but you gotta last just a little longer."

"But it's so hard. I have to keep a brave face around Gary otherwise he'll keep telling me to go on a date with him." Leaf sniffed, and Misty passed her a box of tissues. "Thank you," Leaf muttered. "Why am I even doing this? It's your and Gary's argument. He's really not that bad."

"Leaf! This is proving a point for girls everywhere. It's important. I just wish there was some way to end it…" she trailed off, looking out the window.

"And have you noticed he actually hasn't gone on a date for a month anyway?" Leaf asked.

"That's it!" Misty cried. She turned around to face Leaf. "I know how we can end this."

_**Pokémon**_

"Um, Gary?"

Gary cocked his head towards Leaf. "What's up?"

Her face was red, like she had been crying.

"I can't do this anymore."

He smiled immediately. He knew what she was talking about. Finally, Gary had scored a date with Leaf.

"Five o'clock. This Saturday. I'll pick you up. Wear something nice."

No more words needed to be said. Gary said goodbye and walked down the hallway to his class. He was still smiling.

"Dude, you got it bad." Ash had joined him outside of the classroom.

"Ashy-boy, I don't 'get it bad' over girls."

"Then why have you not dated another girl the entire time Leaf's been dating guys?"

Gary shrugged. "Maybe I am choosing to actually focus on my schoolwork."

"Or, you know how much she hates doing this and you actually did want to impress you."

Gary glared at him. "Bugger off, Ash." He walked into the classroom.

"Not Ashy-boy?" Ash asked.

_**Pokémon**_

Gary picked Leaf up exactly as they had arranged. She had dressed nicely, as he had asked – a knee length, flowing cream dress, a black belt around her waist and black heels. In addition, her hair was straightened and her bangs framed her face.

"Wow," Gary said, upon seeing her.

Leaf said nothing in response. She looked down at the ground, her hands fiddling constantly with her hair and her dress.

"Stop, come on. You don't know how much I've been looking forward to this."

It was the truth. Gary had practically thought of nothing the whole week. All he had wanted to do was plan the perfect date, so that Leaf would no longer think he was such a player. Ash had argued that he did this because he secretly loved Leaf. Gary said he was doing it to prove a point.

In the end, Gary had decided on taking Leaf to the movies, followed by going to a late night sushi train - Ash had informed Gary that Leaf was a vegetarian. Unfortunately, all the places Gary usually went to had heavy, meat dishes.

At the cinema, he invited Leaf to choose the film, and was slightly surprised when she chose the new action film. He had picked her as a 'chick flick' kind of girl.

Then, he reasoned that maybe it was so she did not have to pay attention to him. The movie was certainly action-packed. Neither said a word to each the entire time.

"So, tell me about you, Leaf."

"There's not much to know," she replied. Her hands were still flitting around. She was nervous, Gary could see that, but he had no idea why.

"Is something wrong?" he asked, as they arrived at the restaurant.

"No!" she blurted hurriedly. "I mean, no, of course not. Why should there be?" She said this in a more hushed tone.

"Leaf…"

"It's nothing. Let's just get some sushi."

They sat and ate in silence, occasionally taking plates of sushi off the train.

"You know, this isn't usually how my dates go," Gary mentioned.

"Usually the girl wants to be with you, huh?"

Gary felt a pain in his chest then. He did not think it could have been possible to physically hurt when someone said something like that. Maybe that was how all the girls felt when he broke up with them.

Just then, Leaf's phone buzzed. She looked at it, and then ignored it.

"Should you get that?" Gary asked.

Leaf shook her head. "No, it's fine."

But the way she kept looking at it told Gary it was not fine at all.

"Why were you crying when you asked me out?" he asked suddenly.

"I didn't ask you out," she said.

"Same thing, we're on a supposed date. Why were you crying?"

"It's not the same thing. Really -"

"Leaf."

He was worried, Leaf could tell. After a prolonged pause, she answered him.

"I told you I was sick of it all. That's why I was crying."

"But you were fixing it."

Her phone buzzed again. Before she could pick it up Gary took it, and read the text message.

_Where are you? You're late for our date._

"You had another date for tonight," he said simply. "Maybe you should go to it."

"No. I-"

"I get it. You planned this, didn't you?" He tried to contain his voice to a harsh whisper. "You planned to come on a date with me. So you could let me down and win. You did want to be here. It's alright. I'll go now."

"No, Gary! That's not right." Leaf stood and followed him out the door. Tears were in her eyes. Why had she let Misty talk her into this?

"I'm a slut like you…" she said.

_**Pokémon**_

Word quickly spread around the school about Leaf's date with Gary. Misty could not be more thrilled. The girls all worshipped Leaf. Even some of the guys, who had always had to compete with Gary when asking a girl out, thanked her.

All she could do was mumble to the ground.

In class, her eyes constantly slid to the back of his head. She had lost her friend. He had been that, even though she had not liked to admit it. Despite his flirting, his promise of a date had been a promise that she had not picked up on.

_I promise that when you do not want to go out with any other guy, I will still go out with you. _

He had actually liked her. She learned that on the night of their date.

This felt worse than all of her other dates combined. She remembered going on one such date, and being happy to do it for the cause.

The cause sucked.

There had to be a way to fix this.

She needed Misty. This had all been Misty's idea, she would help her clean up this mess.

_**Pokémon**_

"Gary!"

So used to Leaf calling out his name in the hall, Gary ignored this voice as well.

"Don't make me hit you!"

He stopped. It was not Leaf. It was Misty.

"What's up?" he asked.

"That date between you and Leaf. All my idea. I should have told you earlier. And the text, that was me to. I changed the name on Leaf's phone. I'm just a vindictive, vengeful person but I'm working on that. Ash is the complete opposite of me. Maybe that's why he's going out with me. Anyway," she stopped herself. "I am really sorry. I thought it would be fun, but it turned out horribly."

"I know you're all those things, Misty, but I'm still friends with you. Leaf went along with it, though."

"So you're not mad at me at all?"

"No."

"Oh come on, Gary!" Misty yelled. She hit him. "Don't lie to yourself. Stop lying to Leaf. You have a little bruised ego, now you know how all those other girls felt. Just be honest."

She stalked off down the hall. In truth, he was a little mad at Misty. She had turned the beautiful person Leaf was into a slut like him.

But that was not her fault. It had been the bet, the stupid bet.

As it turns out, they had both won. But they had both lost as well.

"Are you going to talk to me now?"

He was pulled out of his thoughts by the brunette standing by him. She had bright, green eyes, he noticed.

"I don't know what Misty said, well, I do a little bit. She yells really loudly."

Gary could not help but laugh at that. After a little while, Leaf joined in.

"I didn't want to go. I tried to stay," she said.

That was true. She had ignored the phone.

"I know you hadn't dated since the beginning of the bet, and I know that you tried to plan a really nice date. I tried to dress up nice. I even put on makeup. None of that had to do with the bet. What does that tell you?" She smiled a little smile.

Her hands were flitting around nervously. He was reminded of their date. She had done that then, too. Now he understood why.

"You were crying because you didn't want to come on the date with me, because then you would win the bet."

"Yeah." She looked down at the floor. "Really, we both tried to have a good date, with no bet."

"So, it should have been a real date."

"It should have."

"I really like you, Leaf," Gary suddenly said. "I don't just think you're hot…" he trailed off, "Sorry, I'm not real good at this."

"You don't have to be," Leaf said in response. "Look, as far as I'm concerned, there was no bet. We had bad first impressions on our first date, we can fix them on our second. Pick me up at five on Saturday."

She smiled as he nodded.

"Here, let me walk you to class," he said.

They held hands, relishing in the warm feeling that appeared in their hearts when they did so.

Now Gary did not care that their first date had not gone great. It did not matter that either of them now had had many bad first dates.

It did not matter if they were not the first love, the first kiss, or the first date. All that mattered was that they were finding their last.

_**Pokémon**_

**Wow this is terrible haha. I'm sorry. I wanted to try and write a oneshot, and this is how it turned out. The ending is very cheesy, I do not think the characters made that much sense and I could not think I could even put a kiss in for you guys at the end after all I put the characters through.**

**I first thought of the idea while listening to Slut Like You by Pink. It is such an awesome, fun song. Check it out.**

**So, please tell me where I went wrong. Pretty please. I don't care if you review and say 'this sucked'. I just want to know how to improve :)**

**Thank you for reading this. And please check out my other stories, The Mistakes I've Made, and An Oak's Leaf, which are (hopefully) far better than this.**

**Cheers :)**


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